KR960010667A - Sulfonated phosphines, methods for their preparation and use as catalyst components - Google Patents

Sulfonated phosphines, methods for their preparation and use as catalyst components Download PDF

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Publication number
KR960010667A
KR960010667A KR1019950031280A KR19950031280A KR960010667A KR 960010667 A KR960010667 A KR 960010667A KR 1019950031280 A KR1019950031280 A KR 1019950031280A KR 19950031280 A KR19950031280 A KR 19950031280A KR 960010667 A KR960010667 A KR 960010667A
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South Korea
Prior art keywords
sulfuric acid
solution
acid
water
alkyl
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KR1019950031280A
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Korean (ko)
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KR100353331B1 (en
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알바네제 귀도
마네트스베르거 라이너
아. 헤르만 볼프강
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그륀, 페터스
훽스트 아크티엔게젤샤프트
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/5022—Aromatic phosphines (P-C aromatic linkage)

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Sulphonated phosphines of formula (I) are new; where R = 1-4 C alkyl or cyclohexyl; M = H, monovalent metal, chemical equiv. of a polyvalent metal, or opt. alkyl or aryl-substd. ammonium; x = 1-3; and n = 0.1. Also claimed is the prepn. of (I) by reacting tris(o-tolyl) or tris(o-methoxy)phosphine, or their derivs. in which 1-2 aryl gps. have been replaced by R, with an anhydrous sulphuric acid/orthoboric acid system or oleum sulphonating agent.

Description

설폰화 포스핀, 이의 제조방법 및 촉매계 성분으로서의 이의 용도Sulfonated phosphines, methods for their preparation and use as catalyst components

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (10)

다음 일반식의 설포화 포스핀.Sulfosified phosphines of the general formula 상기 식에서, R은 탄소수 1내지 4의 알킬 라디칼 또는 사이클로헥실 라디칼이며, M은 수소, 1가 금속, 화학적 당량의 다가 금속 또는 암모늄 이온이거나, 알킬 치환되거나 아릴 치환된 암모늄 이온이고, x는 1, 2 또는 3이며, n은 0또는 1이다.Wherein R is an alkyl radical or cyclohexyl radical having 1 to 4 carbon atoms, M is hydrogen, a monovalent metal, a chemical equivalent of a polyvalent metal or an ammonium ion, or an alkyl substituted or aryl substituted ammonium ion, x is 1, 2 or 3, and n is 0 or 1. 트리스(o-톨릴)포스핀 또는 트리스(o-메톡시)포스핀 똔느 이들 화합물 중의 하나의 유도체(여기서, 1또는 2개의 아릴 라디칼은 칸소수 1내지 4의 알킬 라디칼 또는 사이클로헥실 라디칼로 대체된다)를 황산.오르토붕산의 무수계 또는 설폰화제로서의 발연 황산과 반응시킴을 포함하는, 제1항에서 청구한 설폰화 포스핀의 제조방법.Tris (o-tolyl) phosphine or tris (o-methoxy) phosphine They are derivatives of one of these compounds, wherein one or two aryl radicals are replaced with alkyl radicals of 1 to 4 or cyclohexyl radicals ) Is reacted with sulfuric acid or fuming sulfuric acid as an anhydrous or sulfonating agent of orthoboric acid. 제2항에 있어서, 설폰화가 황산/오르토붕산의 무수계를 이용하여 20내지 350℃, 특히 20 내지 170℃에서 수행되는 방법.The process according to claim 2, wherein the sulfonation is carried out at 20 to 350 ° C., in particular 20 to 170 ° C., using anhydrous system of sulfuric acid / orthoboric acid. 제2항에 있어서, 설폰화가 황산 중의 삼산화황의 용액, 특히, 용액을 기준으로 하여, 20내지 65중량%의 삼산화황을 포함하는 용액을 사용하여 수행되는 방법.The process according to claim 2, wherein the sulfonation is carried out using a solution of sulfur trioxide in sulfuric acid, in particular a solution comprising from 20 to 65% by weight sulfur trioxide, based on the solution. 제4항에 있어서, 황산 중의 산산화황의 용액이 루이스산(Lewis acid)을 포함하는 방법.The method of claim 4 wherein the solution of sulfuric acid in sulfuric acid comprises Lewis acid. 제5항에 있어서, 루이스산이 붕산인 방법.The method of claim 5, wherein the Lewis acid is boric acid. 제3항 또는 제6항에 있어서, 붕산이 P(Ⅲ) 1몰당 1mol이상 존재하느 방법.The process according to claim 3 or 6, wherein boric acid is present at least 1 mol per mol of P (III). 제2항 내지 제7항 주으이 어느 한 항에 있어서, 설폰화 화합물로 물로 희석시키고, 생성된 수용액을 수불용성 유기용매 중의 수불용성 아민의 용액(여기서, 아민은 황산의 화학적 당량당 0.5내지 3mol의 양으로 사용된다)으로 추출한 다음, 유기상을 분리시키고, 염기의 수용액과 긴밀하게 접촉시킨 다음, 수용성 염기를 분리시키고, 이로부터 설폰화 아릴포스핀을 분리시키는 방법.The method according to any one of claims 2 to 7, wherein the sulfonated compound is diluted with water and the resulting aqueous solution is a solution of water-insoluble amine in a water-insoluble organic solvent, wherein the amine is 0.5 to 3 mol per chemical equivalent of sulfuric acid. Used in amounts), followed by separation of the organic phase and intimate contact with an aqueous solution of base, followed by separation of the water soluble base, from which the sulfonated arylphosphine is separated. 제8항에 있어서, 트리이소옥틸아민이 수불용성 아민으로서 사용되는 방법.The method of claim 8, wherein triisooctylamine is used as the water insoluble amine. 제8항에 또는 제9항에 있어서, 톨루엔이 수불용서 용매로서 사용되는 방법.The method of claim 8 or 9, wherein toluene is used as the water insoluble solvent. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019950031280A 1994-09-30 1995-09-22 Sulfonated phosphine and preparation method thereof KR100353331B1 (en)

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DE4435189A DE4435189A1 (en) 1994-09-30 1994-09-30 New sulfonated phosphines, processes for their preparation and their use as a component of catalyst systems
DEP4435189.5 1994-09-30

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US6307087B1 (en) * 1998-07-10 2001-10-23 Massachusetts Institute Of Technology Ligands for metals and improved metal-catalyzed processes based thereon
US7223879B2 (en) * 1998-07-10 2007-05-29 Massachusetts Institute Of Technology Ligands for metals and improved metal-catalyzed processes based thereon
US6160168A (en) * 1999-02-25 2000-12-12 Bayer Aktiengesellschaft Triphenylphosphine mono and dimethoxy tri-sodium sulphonates
DE19918284C1 (en) * 1999-04-22 2000-12-14 Celanese Chem Europe Gmbh Preparation of aqueous solution of sulfonated arylphosphine, useful in catalysts for hydroformylation of olefins, involves reacting arylphosphine with oleum, diluting and blowing inert gas through the solution
DK1581467T3 (en) * 2002-12-09 2016-11-28 Massachusetts Inst Technology LIGANDS FOR METALS AND IMPROVED METAL CATALYZED PROCEDURES BASED ON THERE
BRPI0617017B1 (en) * 2005-09-15 2016-03-15 Dow Global Technologies Inc process for preparing zwitterionic aromatic phosphine monosulfonate, process for preparing dicyclohexylphenylphosphine monosulfonate alkaline metal salt, and zwitterionic aromatic phosphine monosulfonate
CA2708369C (en) * 2007-12-12 2017-04-04 Massachusetts Institute Of Technology Ligands for transition-metal-catalyzed cross-couplings, and methods of use thereof
BRPI0905700A2 (en) * 2008-01-15 2015-07-14 Dow Global Technologies Inc Complex catalyst composition, complex catalyst or precursor composition, complex catalyst solution or complex catalyst precursor solution, hydroformylation process and class of nonionic triorganofin compounds
WO2009091671A1 (en) * 2008-01-15 2009-07-23 Dow Global Technologies Inc. Sulfonated organophosphine compounds and use thereof in hydroformylation processes
US8461366B2 (en) * 2008-01-15 2013-06-11 Dow Global Technologies Llc Sulfonated organophosphine compounds and use thereof in hydroformylation processes
KR20220056486A (en) * 2020-10-28 2022-05-06 한화솔루션 주식회사 Method for preparing sulfonated arylphosphine

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GB231306A (en) * 1924-03-08 1925-04-02 Moir Buchanan Centrifugal Proc Improvements in or relating to means for the manufacture, centrifugally, of pipes, columns and other hollow articles
US4248802A (en) 1975-06-20 1981-02-03 Rhone-Poulenc Industries Catalytic hydroformylation of olefins
FR2338253A1 (en) 1976-01-13 1977-08-12 Rhone Poulenc Ind PROCESS FOR HYDROCYANATION OF UNSATURATED ORGANIC COMPOUNDS CONTAINING AT LEAST A DOUBLE ETHYLENIC BOND
US4835202A (en) * 1987-11-20 1989-05-30 Ciba-Geigy Corporation (Hydroxyphenyl) phosphine stabilized compositions
DE3942791A1 (en) * 1989-12-23 1991-06-27 Hoechst Ag SULPHONATED PROPYLPHENYL PHOSPHANS, THEIR PREPARATION AND USE
US5481049A (en) * 1993-03-30 1996-01-02 Mitsubishi Chemical Corporation Process for producing alkadienols
TW248563B (en) * 1993-06-29 1995-06-01 Hoechst Ag

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DE59507687D1 (en) 2000-03-02
CN1132208A (en) 1996-10-02
DE4435189A1 (en) 1996-04-04
EP0704450A1 (en) 1996-04-03
US5780674A (en) 1998-07-14
EP0704450B1 (en) 2000-01-26
ATE189223T1 (en) 2000-02-15
ES2143573T3 (en) 2000-05-16
JP2769803B2 (en) 1998-06-25
US5663426A (en) 1997-09-02
CN1051557C (en) 2000-04-19
JPH08176168A (en) 1996-07-09
KR100353331B1 (en) 2003-01-06

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